ES445094A2 - 3,5-disubstituted pyrazoles - Google Patents
3,5-disubstituted pyrazolesInfo
- Publication number
- ES445094A2 ES445094A2 ES445094A ES445094A ES445094A2 ES 445094 A2 ES445094 A2 ES 445094A2 ES 445094 A ES445094 A ES 445094A ES 445094 A ES445094 A ES 445094A ES 445094 A2 ES445094 A2 ES 445094A2
- Authority
- ES
- Spain
- Prior art keywords
- disubstituted
- diphenyl
- reaction mixture
- pyrazolines
- substances
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 3,5-disubstituted pyrazoles Chemical class 0.000 title abstract 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 abstract 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- 150000003219 pyrazolines Chemical class 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- XQEMNBNCQVQXMO-UHFFFAOYSA-M 1,2-dimethyl-3,5-diphenylpyrazol-1-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 XQEMNBNCQVQXMO-UHFFFAOYSA-M 0.000 abstract 1
- JXHKUYQCEJILEI-UHFFFAOYSA-N 3,5-diphenyl-1h-pyrazole Chemical compound C=1C(C=2C=CC=CC=2)=NNC=1C1=CC=CC=C1 JXHKUYQCEJILEI-UHFFFAOYSA-N 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 1
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 235000005513 chalcones Nutrition 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000006356 dehydrogenation reaction Methods 0.000 abstract 1
- 239000004009 herbicide Substances 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 230000020477 pH reduction Effects 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
3,5-Diphenylpyrazole, 3,5-diphenyl-4-alkylpyrazoles or 3,5-diphenyl-4-alkoxypyrazoles are prepared from the corresponding pyrazolines by catalytic dehydrogenation in an inert organic solvent. Platinum or palladium, both of which can also be supported by various substances, can be used as catalysts. The pyrazolines used as starting material can be obtained by reacting a methyl ketone, such as acetophenone or its derivatives, with a suitable aldehyde, such as benzaldehyde, in the presence of a base, to give a 1,3-disubstituted alpha , beta -unsaturated ketone, such as chalcone or its substitution products, acidification of the resulting reaction mixture and treatment of the acidified reaction mixture with hydrazine. The compounds prepared according to the invention can be used as starting substances for the preparation of corresponding 3,5-disubstituted 1,2-dialkylpyrazolium salts, such as 1,2-dimethyl-3,5-diphenylpyrazolium methyl sulphate which, in turn, can be used as herbicides.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/549,219 US3952010A (en) | 1973-09-17 | 1975-02-12 | Catalytic dehydrogenation process for the preparation of 3,5-disubstituted pyrazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES445094A2 true ES445094A2 (en) | 1977-06-16 |
Family
ID=24192112
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES445094A Expired ES445094A2 (en) | 1975-02-12 | 1976-02-12 | 3,5-disubstituted pyrazoles |
Country Status (19)
| Country | Link |
|---|---|
| JP (2) | JPS51101979A (en) |
| AT (1) | AT350549B (en) |
| BE (1) | BE838408R (en) |
| BR (1) | BR7600847A (en) |
| CA (1) | CA1060455A (en) |
| CH (1) | CH608004A5 (en) |
| CS (1) | CS192554B2 (en) |
| DD (1) | DD124249A6 (en) |
| DE (1) | DE2602965A1 (en) |
| DK (1) | DK55276A (en) |
| ES (1) | ES445094A2 (en) |
| FR (1) | FR2300763A2 (en) |
| GB (1) | GB1537859A (en) |
| IL (1) | IL48724A (en) |
| IT (1) | IT1053296B (en) |
| NL (1) | NL178075C (en) |
| SE (1) | SE7601544L (en) |
| SU (1) | SU799657A3 (en) |
| ZA (1) | ZA757986B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3029160A1 (en) * | 1980-08-01 | 1982-03-04 | Basf Ag, 6700 Ludwigshafen | METHOD FOR PRODUCING PYRAZOLES |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5855148A (en) * | 1981-09-29 | 1983-04-01 | Hino Motors Ltd | Production of die for molding |
-
1975
- 1975-12-22 CA CA242,256A patent/CA1060455A/en not_active Expired
- 1975-12-23 ZA ZA00757986A patent/ZA757986B/en unknown
- 1975-12-24 IL IL48724A patent/IL48724A/en unknown
-
1976
- 1976-01-09 IT IT47573/76A patent/IT1053296B/en active
- 1976-01-16 NL NLAANVRAGE7600445,A patent/NL178075C/en not_active IP Right Cessation
- 1976-01-27 DE DE19762602965 patent/DE2602965A1/en active Granted
- 1976-02-03 DD DD191069A patent/DD124249A6/xx unknown
- 1976-02-10 BE BE164196A patent/BE838408R/en not_active IP Right Cessation
- 1976-02-10 JP JP51012890A patent/JPS51101979A/ja active Pending
- 1976-02-10 FR FR7603642A patent/FR2300763A2/en active Granted
- 1976-02-11 SU SU762319859A patent/SU799657A3/en active
- 1976-02-11 SE SE7601544A patent/SE7601544L/en unknown
- 1976-02-11 DK DK55276*#A patent/DK55276A/en unknown
- 1976-02-11 CS CS76899A patent/CS192554B2/en unknown
- 1976-02-11 BR BR7600847A patent/BR7600847A/en unknown
- 1976-02-11 CH CH166976A patent/CH608004A5/en not_active IP Right Cessation
- 1976-02-11 AT AT96276A patent/AT350549B/en not_active IP Right Cessation
- 1976-02-12 GB GB5650/76A patent/GB1537859A/en not_active Expired
- 1976-02-12 ES ES445094A patent/ES445094A2/en not_active Expired
-
1985
- 1985-02-27 JP JP60036705A patent/JPS60222463A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DK55276A (en) | 1976-08-13 |
| ZA757986B (en) | 1976-12-29 |
| AT350549B (en) | 1979-06-11 |
| GB1537859A (en) | 1979-01-04 |
| IL48724A (en) | 1979-07-25 |
| DE2602965A1 (en) | 1976-08-26 |
| IT1053296B (en) | 1981-08-31 |
| NL178075B (en) | 1985-08-16 |
| SE7601544L (en) | 1976-08-13 |
| CH608004A5 (en) | 1978-12-15 |
| DE2602965C2 (en) | 1988-11-17 |
| FR2300763A2 (en) | 1976-09-10 |
| AU8790475A (en) | 1977-06-30 |
| JPS51101979A (en) | 1976-09-08 |
| CS192554B2 (en) | 1979-08-31 |
| BR7600847A (en) | 1976-09-14 |
| JPS6227068B2 (en) | 1987-06-12 |
| FR2300763B2 (en) | 1982-09-03 |
| CA1060455A (en) | 1979-08-14 |
| JPS60222463A (en) | 1985-11-07 |
| SU799657A3 (en) | 1981-01-23 |
| NL178075C (en) | 1986-01-16 |
| NL7600445A (en) | 1976-08-16 |
| IL48724A0 (en) | 1976-02-29 |
| DD124249A6 (en) | 1977-02-09 |
| BE838408R (en) | 1976-08-10 |
| ATA96276A (en) | 1978-11-15 |
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